Condensation product of acrolein and process of producing the same



Patented Nov. 16, 1926.

UNITED STATE-S PATENT OFFICE.

CHARLES IOUBEU AND CHARLES DUI'BAISSE, OF PARIS, FRANCE.

CONDENSATION PRODUCT OF ACROLEIN AND PROCESS OF PRODUCING THE SAME.

R0 Drawing. continuation or application Serial No. 433,884, filedDecember 28, 1920.' .lh-il application flied March 29, 1922, Serial No.547,919, and in France larch 81, 1919. i-

(GBANTED UNDER THE PROVISIONS 0! arm ACT 01 IABOI 3 1921, 41 STAT. L,1313.)

Patents containing the disclosure corresponding to the presentapplication have been obtained as follows: France, March, 1919; Belgium,March 2, 1920; Italy, May 7, 1920; England, March 31, 1920; and Germany,March 18, 1920.

This invention relates to a process of preparing a resin from acroleinwhich can be employed as a hard and insulating varnish or for themanufacture of various objects, the present application being acontinuation of our earl er application bearing Ser. No. 433,664, filedDecember 28, 1920.

The preparation is made by direct condensation of substant allyanhydrous acrolein in asingle stage with a suitable phenol in presenceof a trace of a suitable reagent, for instance a mineral or organic baseeither free or combined.

The present invention differs from that described in our copendingapplication Serial No. 433,664, filed December 28, 19:20, in whichacrolein itself is condensed by traces of resinitying agents such asalkaline carbonates, salts of heavy metals, ammonia, methylamine,aniline, ferric chlorid, and acetate of lead yielding resins. Proceedingaccordin to the disclosure in our copending appllcation, it issufiicient to dissolve the acrolein in water and to add the resinifyingreagent in order to obtain a voluminous white precipitate which, whenwashed and dried in vacuo, forms an impalpable white powder insoluble inwater and hydrocarbons, but

' very soluble even in the cold in the majority of other organicsolvents and particularly in alcohols, ketones and acids.

This product agglomerates and melts forming a viscuous mass at avariable temperature depending on the conditions of preparation, butusually between 80 and 110 C. Its other physical properties also dependupon the conditions of preparation.

On evaporating the solvent, solutions of this product leave a verybrilliant and perfectly limpid varnish which can be em loyed in anysuitable manner for the usua purposes for which products of this kindare employed in simple or multiple layers by coating or dipping forexample on surfacesof all kinds such as metal, wood, celluloid. and forvarious purposes such as insulation or protection against corrosion andso on.

It has been proposed to manufacture synthetic resins by treating variousaldehydes arated and allowed to stand till more water separates out. Inthe third stage the product is heated to expel all traces of water andthe catalytic agent.

The reaction according to the present inventlon is extraordinar lysimple since the acrolein and the phenol are simply mixed with a smallquantity of the condensing agent when the reaction takes place so as togive a 100% yield.

Example.

parts of commercial phenol and 90 parts of anhydrous acrolein aretreated with 1 part of caustic soda. A reaction takes placespontaneously at ordinary temperatures but can be acce erated byheating, not above 100 C. The reaction is complete, with 100% yield whenthe mass has reached the desired consistency.

1n the process according to the present invention, the proportions ofacrolein and phenol can vary within very wide limits, e. g. from 90% asin the above example acrolein to 20% acrolein and even less.

Instead of using acrolein itself as raw ma terial, a suitable resin orpolymerization product thereof may be employed. In this case it isnecessary to warm the mixture in order to prepare the condensationproducts with phenol.

On the other hand however it is also possible to dissolve the acroleinresins and the phenol in a suitable solvent which is then allowed toevaporate, or the two substances are melted together at a temperaturenear 100 C. It is also possible to employ a solution of acrolein resmsin acrolein itself.

Obviously phenol itself can be replaced by any other suitable bodycontaining a phenolic group, e. g. simple plhenols such as cresol, ornaphthols, or poly ydroxy bodies such as guaiacol or eugenol.

The resins obtained according to the present invention are hard, cannotbe scratched with the 1. A condensation product resulting .fromthereaction of a phenolic body and acrolein, consisting of a dense,homogeneous solid infusible at all temperatures-and insoluble inalcohol, acetone, benzol and other ordinary organic solvents.

2. A condensation product resulting from the reaction of phenol andacrolein consisting of a resinous material. A

3. An initial condensation product resulting from the reaction of aphenolic body and acrolein and consistin of a liquid soluble beingfurther condensed and soli fied by so heating.

4. The method which consists in causing a phenolic body and acrolein toreact to form an initial condensation product capable of bemg furthercondensed and solidified my 25 heating.

. -5. A process of obtaining an insoluble hardand non-conducting resinwhich consists in condensing acrolein with phenols directly in. thepresence of a trace of a catalytic or con- 30 densmg agent.

' Signed at Paris, France, this 10th day of February, 1922.

CHARLES MOUREU. CHARLES DUFRAISSE.

